Carbon tetrabromide → HCID 86699391, compound

HRID 925319Notes

Reaction equation

HRID 925319 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:5]2[CH2:19][CH2:20]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:41]C(Br)(Br)Br>C1COCC1>[Br:41][CH2:20][CH2:19][C:5]1[C:4]2[C:8](=[CH:9][C:10]([Cl:11])=[C:2]([Cl:1])[CH:3]=2)[NH:7][C:6]=1[Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 679733232-(5,6-Dichloro-2-(triethylsilyl)-1H-indol-3-yl)ethanol

Product 1

HCID 86699391HCID 86699391, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(2-bromoethyl)-5,6-dichloro-2-(triethylsilyl)-1H-indole was prepared according to method D Step III with 2-(5,6-dichloro-2-(triethylsilyl)-1H-indol-3-yl)ethanol (1.7 g; 4.94 mmol) in THF (6 mL) and triphenyl phosphine (2.59 g; 9.87 mmol) and perbromomethane (3.27 g; 9.87 mmol) in THF (40 mL) pre-stirred for 30 minutes. The crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to yield 0.548 g (27%) of 3-(2-bromoethyl)-5,6-dichloro-2-(triethylsilyl)-1H-indole as a brown oil.

Workup

  1. custom3-(2-bromoethyl)-5,6-dichloro-2-(triethylsilyl)-1H-indole was prepared
  2. customThe crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-f4b6a5480d954e3fb9ba20563f8568c6
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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